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Lifestyle Personal Finance

How to Manage Debt The Year Before Buying a Home

The whole value of the dime is knowing what to do with it.

Ralph Waldo Emerson (1803-1882)

The most frequently asked questions I get from my students (especially the boys) are related to personal finance or financial literacy. As someone who’s pretty passionate about finances, I figured it would be fun if I started to share my knowledge and experience and created a place for students to come and learn financial literacy.

This wasn’t something I planned on doing for a while, but Katie approached me with an idea for collaboration so I figured this would be a good starting point.

The article is written by Katie, but I chime in with a few thought of my own after CM:


Written by Katie Conroy of advicemind.com

Right now, low-interest rates are extremely appealing to many hopeful home buyers. However, we aren’t all in a solid enough position to buy a house right now. Debt is extremely common, and many of us would prefer not to take on more before reducing what we already have. Plus, credit scores aren’t exactly known for treating people with a ton of debt kindly. 

Fortunately, there’s a lot that can be done to make debt more manageable. There’s no reason that debt has to stand in the way of homeownership. Here are some tips to inspire savvy debt management and strong financial decisions in the months leading up to buying a home: 

Get Informed 

When it comes to any financial endeavor, knowledge is our very best asset. Credit scores, though an imperfect representation of someone’s full financial health, are an excellent starting point when it comes to building this knowledge. There are plenty of sites online that give free access to credit scores. With this information, we can come to better understand our starting position, and make wise choices about how to proceed. 

Remember, bad credit does not necessarily mean buying a house is off the table. It can mean that we need to take steps to improve our scores or look into alternative lending options. For example, there are plenty of loan programs out there designed to help those with small down payments or poor credit scores be able to buy a home. Looking into these programs and figuring out the available options can help make the next steps clearer.

CM: If possible, I say plan on doing whatever you can to boosting your credit score. Buying a home is a big-ticket purchase, often the most expensive things most people buy in their life. I suggest shooting for the bottom of the highest tier (at least 800), this should qualify you for the best rates. If that is too far away, a 670 would get the job done in most places. Planning for massive purchases can save us thousands down the line.

Boost Monthly Payments 

One simple way we can put ourselves in a better position for home buying is to reduce that debt load. Paying more into the principal of a loan comes with a number of benefits. It can make monthly payments smaller, improve credit scores, and reduce the amount of interest that gets added back into the principal over time. 

Plus, taking this extra load on is great practice for homeownership. Although the monthly payment for a loan itself is often less than rent in the same area, that’s not the only thing that contributes to month-to-month costs for homeowners. Insurance, taxes, and utilities can mean that owning a home costs as much — or sometimes, more — than renting. When we pay more out on our debt, we practice living with higher payments and less extra spending to go around. This puts us in a far stronger position when it comes to managing finances down the road.

Make a Clear, Actionable Plan 

When it comes to any major undertaking, our best roadmap is a clear, detailed plan with actionable steps to guide our path. The first step is taking a clear look at our current financial situation, including all income sources, savings, and debts owed. Next, it’s figuring out exactly how much we can manage to put each month toward shifting those balances in our favor. Then, we have to ask ourselves the hard questions, such as, “Can I commit to this? Is it feasible? Is it what I really want?” 

Once these questions have been answered, we’ll have a solid direction in which we can move. Homeownership is one of life’s most exciting milestones, and debt shouldn’t have to stand in its way. Increase payments, boost savings, and do the work necessary to make this dream come true. 

CM: This is so true. Nothing works without a plan. Trust me, I’ve tried to make it work. My favorite financial plan is known to many as Conscious Spending, made popular by Ramit Sethi. This plan involves spending extravagantly on what I love and cutting spending intensely on everything I don’t care for. This prevents me from spending any money on unnecessary things. After practicing conscious spending for about a year, I saved more money and lived more of my “rich life” than I ever thought possible. This plan may not work for everyone, but it works great for me. Having a plan is crucial, we just need to find which plans work best for us.

Categories
Education Productivity

Analyzing & Improving Systems

“If you are unhappy, your system is broken.”

Brandon Turner (The Book on Rental Property Investing)

In my last post, I talked about Gall’s Law and the different components of systems. In this post, I’m going to discuss ideas surrounding analyzing and improving systems. There are going to be some terms I reference from my last post, so I highly recommend checking that out first.

Josh Kaufman beautifully and simply explains how to do this in his book, The Personal MBA, and I also highly recommend checking that out too. The ideas in this post are mostly from that book as well as my own personal insights.

How to Analyze Systems

When analyzing a system is difficult to know what to look for, especially when dealing with complex systems. It’s also crucial to keep in mind that we all have a bias which could get in the way of analyzing systems. Whenever possible, we need to take steps to mitigate our bias.

Here are some other things to look out for when analyzing systems:

Deconstruction

This is an excellent first move when it comes to analyzing systems. As discussed in Gall’s Law, all complex systems arise from simpler systems, therefore every complex system is capable of being deconstructed into simpler systems. Deconstruction is simply breaking up complex systems into their interdependent parts and understanding how each of those parts works. It’s also helpful to try to identify triggers (what kicks off another system) and endpoints (what makes a system stop). Diagrams and flowcharts are also lifesavers when it comes to deconstructing systems. Recognizing if-then and when-then relationships are also invaluable.

After breaking the complex system up into it’s smaller parts, we can then break down those simple systems even further into their components. Identify inflows and outflows, stocks, interdependencies, and so on. I talk about what those components are in my last post.

Deconstruction makes understanding systems possible. Without deconstruction, we are sure to experience confusion.

Measurement

How does the system collect data? What kind of data is it collecting? Measurement describes the process of data collection in a system. If we can understand the information related to the system, then we get an insight into the system itself.

Paying attention to the measurement is fantastic for dealing with absence blindness — the idea that we have a hard time seeing things that aren’t there.

Let me give an example, measuring someone’s blood glucose levels tells us if someone has too little or too much blood sugar. This number gives us tremendous insight into what is going on inside the body even though we wouldn’t be able to visibly see changes in someone’s blood sugar.

Measuring something is the first step in improvement. I wrote a post, Tracking vs. Loss Aversion, that talks about the importance of measuring ourselves and our progress.

Don’t sleep on measurements. Trust me.

KPI (Key Performance Indicator)

I know I just emphasized how important it is to measure things, but there is such a thing as too much data. If we measure too many things, we end up having a bunch of junk data that weighs us down and doesn’t show us anything. In order to prevent this, we try to keep our measurements to only KPIs or Key Performance Indicators.

KPIs are measurements of the essential parts of a system.

Identifying KPIs can be tricky, but try to limit them to only 3-5 KPIs per system otherwise, we risk measuring too many things.

Garbage In, Garbage Out

This is one of the more straightforward ideas – what we put in is what we get out. The quality of the output is only as good as the quality of the input. You get what you give. There are so many cliche phrases that express this idea.

I found this to be especially true when I started cooking. I used to watch Gordon Ramsey cooking videos to try to learn how to cook (I even watched his Masterclasses), but I could never make my food taste good until I spent the extra money on fantastic ingredients. Now, I try to only cook with fantastic ingredients. It really makes all the difference.

One of the best ways to improve the quality of a system is to pay attention to what we start with.

Tolerance

This can be thought of as the range in which the system is working normally. If the system is performing within that range, then it’s within tolerance.

Tolerance can either be loose or tight. A loose tolerance is when there is a considerable amount of leeway and small mistakes don’t make a huge difference while a tight tolerance is when there’s little room for error or change, this is usually the case for essential components of a system.

Analytical Honesty

In order to properly analyze a system, we must acknowledge our propensity to make things look better than they are. We have to be able to apply objective judgment to our data which means that the best analysis of a system will come from someone who isn’t personally invested in it.

As I mentioned in my post, Our Unconscious Filters, human beings view the world through their bias and it’s hard to shake them, even if we’re aware of them. Having an outsider provide analysis is the only way to completely prevent our bias from contaminating our observations.

Context

Most measurements are meaningless without context. Context is all of the information we use to understand if measurements are favorable or not. Setting goals for arbitrary numbers like a 20% increase or 3 new deals are meaningless if we don’t know the performance of the system in the past and it’s projected performance in the future.

Trying to oversimplify how a system operates by judging it off one measurement will blind us to other important changes as well. Context is crucial for an accurate understanding.

Sampling

Sampling is what we do when we try things. We’re simply taking a small part of the output and using it as an example for the entire system. Sampling is great for catching errors without needing to check the entire system.

Just like all other methods of analysis, we have to consider our bias, and sampling is prone to bias. A way to control for it is to make sure the sample is random.

Margin of Error

Of course, not all samples will be perfect representations of the entire system. The margin of error is how much the sample deviates from the whole. The higher the margin, the more inaccurate the sample. The more samples we have, the smaller our margin of error.

Ratio

Ratios are fractions. Somethings divided by something else. It’s a simple way of measuring multiple variables at once. Ratios are also great for letting us know how a particular measurement changes.

For example, ROI is a percentage ((Returns/Investment)*100%) or comparing MPG (miles/gallons) or unit price of groceries. You know a ratio is involved in you hear the words per.

Typicality

In order to analyze a system properly, we need to know how it would operate normally. Kaufman suggests that we can measure typicality through calculating mean, median, mode, and midrange or various measurements.

Correlation & Causation

Causation comes from the idea of cause and effect. One part of a system is causing another part of a system to act. Correlation, on the other hand, is not always causation. Sometimes variables may seem the act like one causes the other, but that won’t necessarily be the case. For example, 100% of people who drink water die. Does the water cause the death in this case? Probably not. Water and death are simply correlational.

So how can we determine is something is correlational or causational?

By adjusting for known variables. If we control for as many variables as possible, we can see the relationship between each more clearly. As systems grow more complex, this becomes more and more difficult. The more we can isolate a variable, the more confidence we have that the changes are causational.

Proxy

Proxies are measurements of something by measuring another thing. A proxy is useful when we cannot measure something directly. The closer the proxy is to the original, the more accurate the measurement. We have to be mindful about correlation and causation when measuring a proxy.

Segmentation

Segmentation is grouping data into separate subgroups to get a more comprehensive context. I do this with all of my blog posts! That’s why I have titles and headings and subheadings. It gives all the (seemingly) random information I’m spewing a more detailed context.

Segmentation plays a huge part in how we understand complex and large amounts of information.

Humanization

When looking at data is easy to see it as an inanimate object, but when analyzing systems we have to keep in mind that the data tell us information about human beings. They are insights into real people — their behaviors, experiences, and thoughts. It’s easy to disconnect from data about a system because it seems so abstract and inanimate, but it’s quite the opposite. If we pay enough attention, the data lets us understand people on a deeper level.

When I worked at Kohls, they always emphasized selling to “her.” Her being a personified collection of the average data on their customers. They used average household income, gender, family size, and other variables to create their typical customer and found ways to satisfy that person.

Our data tells us what’s up with other people if we look hard enough.

Other Things to Look Out For

“If something in your business is causing you stress, most likely, you either don’t have a system for that issue, or you are not following your system.”

Brandon Turner (The Book on Rental Property Investing)

Pay attention to environmental changes and selection tests. I talk a little bit about these in my last post. These changes give smaller players a chance to outperform larger players. Identifying selection tests gives us a competitive edge.

Some questions to ask while looking out for these things could be: How is the environment changing? Who is unable to adapt to these changes? What can I do differently from those who cannot adapt? Who is taking advantage of these changes? What can I do similar to those who are doing well?

Always keep an eye out for the “black swan.” I first heard about this idea from Chris Voss, an ex-FBI terrorist negotiator. The “black swan” is any information that if discovered would change everything. Back in the day, people would say swans are white and if anyone said otherwise they would be crazy because swans are white. Eventually, someone discovered a black swan and everyone had to change how they saw the situation. Systems are the same way, try to keep an eye out for the information that would change everything. There’s always a piece of information that, if known, would change everything This is excellent for accurately identifying and balancing risk and uncertainty.

It’s also helpful to keep in mind that we process the unknown the same way that we process threats. We literally see and respond to what we don’t know as a threat. Expect to encounter threats, but instead of responding to it, we can respond with curiosity to learn more.

The last thing I want to mention about analyzing systems is to analyze close-calls when they happen to minimize accidents. Sometimes shit happens, but most of the time we can prevent it from happening. If we can notice when things almost go wrong, then we can take the steps to make sure that it doesn’t happen again or prevent the conditions that allowed it to happen in the first place without having to deal with the fallout of the accident.

How to Improve Systems

“Anyone who understands systems will know immediately that optimizing parts is not a good route to system excellence. For example, let’s build the world’s greatest car by assembling the world’s greatest car parts. We connect the engine of a Ferrari, the brakes of a Porsche, the suspension of a BMW, the body of a Volvo. What we get, of course, is nothing close to a great car; we get a pile of very expensive junk.”

Donald Berwick (1946 – )

Now that we’ve discussed analyzing systems and have a base framework for understanding systems, let’s talk about some of the ideas useful for improving systems. Most of these ideas are also included in Kaufman’s The Personal MBA.

Intervention Bias

This is the idea that human beings tend to add changes to a system just to feel like we have more control. So when we set out to improve a system, we have to entertain the thought that we might be implementing a new change just to feel in control. If we don’t, we risk adding unnecessary complexity to the system.

The best way to account for intervention bias is to analyze through a null hypothesiswhat would happen if we did nothing? What if the situation was simply an error?

If the null hypothesis experiment determines that we’re better off doing something than nothing, then we will have minimized our chances for intervention bias to take hold. Examining the null hypothesis isn’t our natural reaction, especially since human beings have a proclivity to doing something rather than nothing, but it’s crucial for actually improving systems.

When improving systems, first think about what would happen if we did nothing.

Optimization

Optimization is what people usually think of when it comes to improving systems. This typically involves maximizing output or minimizing an input. Optimization is usually focused around the KPIs.

Kaufman suggests when optimizing a system to focus on one variable at a time. Optimizing a system across multiple variables will almost always lead to disaster. System interdependencies and second-order effects make it challenging to change more than one thing at any given time.

Refactoring

This refers to changing a system’s process so that it can perform the exact same result but in a more efficient way. This is most obvious in coding. Some programmers will pride themselves on performing the same actions in fewer lines of code.

To the average person, refactoring may seem insignificant, but more efficient systems run faster and require fewer resources which could be redirected elsewhere.

Some questions to ask when refactoring a system could be: What are the essential processes to achieve the desired objective? Do these processes have to be completed in a certain order? What are the constraints of the system?

Critical Few

If you’ve heard of the Pareto Principle (a.k.a. The 80/20 Rule), then you understand the concept of the critical few. Essentially, 19th-century economist and sociologist, Vilfredo Pareto, discovered an interesting pattern when analyzing data regarding land ownership and wealth distribution.

He discovered that 80% of the land was owned by 20% of the population. Pareto didn’t just find this pattern in wealth and land distribution, he also saw it in his garden. 20% of his pea pods produced 80% of the peas.

Today, we can see his 80/20 split in almost everything. In systems is useful to know that 80% of the output is from 20% of the input. In businesses, typically 80% of revenue usually comes from 20% of customers. 80% of the work is done by 20% of the people. 80% of our time communicating is with 20% of people we know.

Focus on the 20%. That is where the biggest changes will happen. Identify which parts are critical and give it attention or starve it of attention, whichever is required. The idea is to not try to focus on the whole thing, but the smaller parts that matter.

I do this with my students. 80% of my income comes from 20% of my clients and my attention and efforts are split accordingly. I give the clients who matter more attention and I starve the ones who don’t. After practicing these methods, I’ve eliminated a lot of headache clients and I’ve strengthened my relationships with the ones I do like. 80% of the problems came from 20% of the clients.

Focus on the critical few.

Diminishing Returns

This is the idea that after a certain point, adding more starts to cause more harm than good. This is common when optimizing high performing systems, people tend to try to push the system even more to the point where the system breaks.

“The last 10 percent of performance generates one-third of the cost and two-thirds of the problems.”

Norman R. Augustine (Aerospace Executive & Former U.S. Under Secretary of the Army)

A way to control for diminishing returns is to apply Ramit Sethi’s infamous “85% Solution” from his fantastic book I Will Teach You To Be Rich. Simply get 85% of the problem right and move on. Yeah, we can really hone in on getting that extra 15%, but then we risk diminishing returns.

Is it worth doubling the effort just to squeeze out that extra 10-15%?

It might be, but not every time. It’s better to spend our energy getting the big wins, than trying to squeeze out every little bit.

Friction

Friction is something I pay a lot of attention to. I spend a lot of time dedicated to removing friction from my life because it stops me from doing so much. Friction is any force or process that removes energy from a system. Remove the friction, increase efficiency.

Amazon Prime is a perfect example of a company removing friction to make a system more efficient. If you have amazon prime, then you know how easy it is to purchase things. That’s intentional. The ease of use creates more cash flow for the business.

If a system has a lot of friction, it can still perform but it will require much more energy. If we don’t add more energy, then the system will eventually slow and stop.

For me personally, when I encounter friction while doing an activity that I don’t enjoy, then I won’t do it at all. So if I can help it, I try to remove as much friction as possible whenever I’m doing something difficult or something I don’t want to do.

Sometimes introducing friction is what’s needed to improve a system. When I want to prevent myself from performing certain actions, I introduce friction because I know it will stop me. Some business makes it cumbersome for a customer to return their product so they are less likely to return it.

Automation

The gold standard of no friction. Automated systems operate without human intervention. Automation is best for repetitive tasks.

Be mindful that automating a system tends to magnify the efficiencies and inefficiencies. If the system is already efficient, then automation will make it faster. If the system is not efficient, then automation will slow it down.

When it comes to understanding automation, we want to be familiar with the Paradox of Automation: the more efficient an automated system is, the more critical the human inputs are. While automate reduces the need for human intervention, the small amount of human intervention that occurs becomes increasingly significant.

Automation makes our actions count more, not less.

On that note, I also want to mention the Irony of Automation: the more reliable a system is, the less attention humans pay to it. Reliable systems train absentminded operators. This is dangerous because if something goes wrong, we aren’t likely to notice and the automation will propagate that error.

The best way to avoid automation errors is to perform consistent sampling and testing.

Standard Operating Procedure

SOPs are predetermined processes for completing certain tasks or solving common problems. We save cognitive load and cut down the number of decisions we have to make in a day if we have a preselected method that’s known to work.

Using SOP helps us spend our energy on improving a system, rather than solving repetitive problems over and over.

Kaufman recommends reviewing the SOPs every two to three months to keep it running effectively.

SOPs can look many different ways. For example, I have a set price for certain students, and certain times I will tutor. But it can go further than that, I have predetermined phrases that I say when talking to clients to make communication easier when it comes to scheduling or other common tasks. I also have predetermined methods for dealing with certain kinds of students so we have a simple system for us to start with and build upon.

Focus on creating go-to methods for things you encounter often. You’ll find that it can seem like a lot of work upfront, but it will streamline the process in the long run and it’s so worth it.

Checklists

I can’t talk about checklists without referencing Dr. Atul Gawande’s The Checklist Manifesto. That book beautifully describes the power of checklists. Checklists have been a vital part of pilots take off routines and are the reason for their high success rate. Checklists have also played their role in minimizing infection rates in hospitals all over the world. The secret to repeatedly completing complex tasks perfectly is writing it down as a checklist.

Checklists are simplified SOPs for specific tasks. They’re fantastic because they create systems for processes that haven’t been articulated and minimize our chances of skipping critical steps.

I always make a checklist for my students who are struggling to “manage the chaos.” Transforming the glob of craziness that is school work into a list that can help us narrow our focus works for every single student I have ever worked with. Seriously, I haven’t come across any academic situation that a checklist could not solve.

Checklists are so critical for entropy management that I use them whenever I’m feeling overwhelmed. Whenever I’m feeling stressed and swamped with work, I ask myself “What’s the 80/20 I need to tackle here?” then I made a checklist to conquer the critical few.

I’ll probably write another post on checklists because they’re so damn powerful, important, and useful.

Checklists are also great because once we have a good one, we can delegate or automate it — which frees us up from doing the work! Checklists tend to be the first step to freedom.

Cessation

This refers to the idea of stopping something intentionally. Sometimes a system may be going haywire and the best thing to do is to stop a process. As I mentioned earlier, humans have a proclivity to do something to improve a system, but sometimes the best choice may be to not do anything or stop altogether.

Cessation is not our natural reaction when we want to improve systems and it’s usually an unpopular choice when dealing with a group, but keep in mind that it’s a valid option.

When analyzing and improving systems, I entertain the idea of cessation after I’ve tried the null hypothesis. If both of those options are determined to be ineffective, then I’ll start doing something to improve the system.

Resilience

The resilience of a system is determined by how much change it can withstand. The ability to weather change and adjust plans means the difference between disaster and survival.

Resilience usually comes at the price of optimal performance. A system can increase its resilience through leverage. For example, if a business needed some money to weather the storm it will be more resilient, but that money can’t be used more efficiently. Resilience comes at a cost.

Another way to boost resilience is to prepare for the unexpected. Having plans for different/unexpected scenarios or extra supplies on hand are great ways to make a system more resilient. Fail-safes and backups are great for that also. A fail-safe is a backup system designed to prevent or recover from the original system failure.

Stress Test

This is the process of identifying the boundaries of a system by changing the environment. Testing different extremes on a system can help determine which variables affect which processes.

When I stress test my systems, I try to break them. This is the part when we want to try and test out our “what-if” scenarios. Scenario planning is at the heart of any effective strategy. Rather than trying to predict the future, we can prepare for a handful of imagined scenarios and be ready for what comes next. A proper stress test can really help with a system’s resilience.

Sustainable Growth Cycle

This cycle is a pattern that systems follow when undergoing consistent growth without any major issues and it’s split up into three phases:

The Expansion Phase – this is when the system is focused on growing. This is a creation phase. New components and strategies are implemented and dedicated to growing the system and collecting data.

The Maintenance Phase – this is when the system focuses on executing the strategies and maintaining the functionality of the system. Pressing play on the system, so to speak.

The Consolidation Phase – this is when the system is focused on analysis. All the data that was collected is now put into context. Things that work are given more resources and attention while things that don’t are cut back or reworked.

The Middle Path

This idea comes from the fact that the balance between too much and too little are constantly changing. Balancing what systems need requires constant reevaluation. The best approach usually lies somewhere between too much and too little.

Experimentation

No one has everything figured out and determining the best choice when it comes to improving a system is a difficult task. This is when experimenting comes in handy. Frequent experimentation is the only way to accurately determine what improves and system and what doesn’t.

I like to treat experimenting is play. I love trying to new things, changing stuff up, and seeing what happens. The more we experiment, the more we learn about our systems.

More Methods of Improvement

“A man with a surplus can control circumstances, but a man without a surplus is controlled by them, and often has no opportunity to exercise judgment.”

Harvey S. Firestone (Founder of the Firestone Tire and Rubber Company)

A personal note for improving systems – I like to have stock built up for projects with continuous deadlines like blog posts and beats. Having more stock makes me less anxious about meeting a deadline and I can focus on making good music or writing a good post. To increase stock, simply increase inflows and decrease the outflows. In this case, I increased how many beats I made in a week, but released only 1 (I usually release 2). After a while, I started to build a stock and the beats I made later were of higher quality. My end goal is to make high-quality music while enjoying the process, so I modified my system to make that happen.

In every system, there’s always a limiting reagent. Finding that constraint and removing it will improve a system’s efficiency. Israeli author, Eliyahu Goldratt, suggests using the “Five Focusing Steps” to identify and eliminate constraints:

  • Identification – examining the system to find the limiting factor
  • Exploitation – ensuring that the resources related to the constraint aren’t wasted
  • Subordination – redesigning the entire system to support the constraint
  • Elevation – permanently increasing the capacity of the constraint
  • Reevaluation -after making a change reevaluating the system to see where the constraint is located

When dealing with systems that involved other parties, we introduce counterparty risk. The best way to deal with counterparty risk is to have a plan of action in the event that the other party doesn’t deliver on their end of the deal.


These ideas are foundational for analyzing and improving systems but the methods are endless and I recommend that you go out and find concepts and methods to build upon your knowledge of systems. Remember Gall’s Law, all complex systems evolve from simple systems, and these ideas are the components of creating a simple system to analyze and improve other systems. How meta.

However, the most important concept for analyzing and improving systems is understanding that we can always learn more and education never stops. Systems can be complex and there is always something more to learn about a system or systems in general

Categories
Education Lifestyle

My Must Read Book List

“A reader lives a thousand lives before he dies . . . The man who never reads lives only one.”

George R.R. Martin (1948 – )

Here’s a list of all the books that had a massive impact on my life and would bring tremendous value to everyone else too – in no particular order:

Laws of Human Nature (2018) – Robert Greene

This is hands down one of the best books ever written. When I read the title, I thought it was too ambitious to try to capture human nature in a book but Robert Greene was the perfect man for the job and he did it fantastically. Greene beautifully outlines the underlying forces that control our behavior and gives us the tools to recognize them within ourselves and others. After reading this book, I was given new insights on what really drives human beings and the pitfalls that we should be aware of as we navigate life. I was especially impressed and surprised with the chapters on narcissism and envy. Greene opened my eyes to how deep those two forces run in our society today and how dangerous it can be. I went to a book signing when it was first released and Robert said it’s important to read this book as as insight into ourselves rather than as insight into other people. I cannot say enough positive things about this book. Right now, it’s my #1 most recommended book for everyone to read. Buy a copy for yourself. Buy a copy for someone you really care about. Then buy another copy for someone they care about. This book is too important to skip over.


Outwitting the Devil (1938) – Napoleon Hill

Napoleon Hill is the O.G. when it comes to writing about success. OTD isn’t as popular as Hill’s best seller, Think and Grow Rich, but it shares many similar themes. The concepts that Hill uncovers in this book laid the foundation for a majority of my own personal development. Styled as an interview between an intelligent human and the devil himself, Hill captures how the devil is very much alive and well in our world — just not in the way that we think. Idle hands truly do the devil’s work. He cautions us of the dangers of being a drifter, the power of definitive purpose, independent thought, and hypnotic rhythm. A fantastic read for anyone who wants to get into reading and doesn’t know where to start. This book really helped me out when I first got out of college. It really gave me the tools to outwit the devil that I didn’t even know I was battling.


Tao Te Ching (~4th Century BC) – Laozi

This ancient Chinese religious text details the common principles of Eastern thought. A must read if you want to live well. The wisdom written in this book is timeless. The book itself is a practice of minimal necessary effort. So it’s a short, easy, but deep read.


Show Your Work! (2014) – Austin Kleon

This book is so great for creative types who have trouble putting their work out. It’s also great for those wondering how to get their creative endeavour started. It’s given me new and fantastic perspectives about creativity and what it means to make art. We should all strive to be amateurs – Sharing my art inspires others and contributes to the culture around me – No one artist or genius was created in a vacuum. This book has shown me countless ways to be inspired by and inspire others. It’s also filled with creative methods from so many unique creative types. If you want to unleash the creative side of yourself – read this book.


Lord of the Flies (1954) – William Golding

Lord of the Flies is a masterpiece. It’s about a group of boys stranded on an island and their attempt to govern themselves. Golding perfectly nails the complexities of the human spirit. He captures the everlasting struggle between our desire for order and tendency for chaos. This book is gripping and perfect for anyone looking for a good story. Even putting the themes aside, the plot is interesting and the characters are lovable. This was one of the first books that opened my eyes to the power of reading. For the first time, I saw that characters in a book can be as complex as people in real life. I used to think characters in books were just representations of the author, but Golding showed me that people can put enough thought and care into a book and create a literary mural that represents humanity.


The 48 Laws of Power (1998) – Robert Greene

I think about this book at least four times a week. This is the book that Andy from The Office should have read to truly win over Michael Scott. This was Robert Greene’s first book and it took the world by storm. He explains each of the 48 laws of power with examples from history of how each law can be used to one’s advantage and disadvantage. In his early days, similar to Benjamin Franklin, Robert Greene found himself getting the short end of the stick on many situations. He took his intense frustration and anger and articulated each and every trick that his superiors would use on him. This book helped me understand the power plays used on me in the past but the best part, is being able to spot the power moves others try to pull on me now. The world belongs to those who read.


Poor Richard’s Almanack (1732) – Benjamin Franklin

Benjamin Franklin is one of my favorite people in history. He’s accomplished enough for 10 men and in Poor Richard’s Almanack he lays out his basic principles which set the foundation for his success. I love this book because the principles are so simple and, for the most part, common sense. It’s essentially a list of 670 nuggets of wisdom. Most people link the famous idioms “Early to bed and early to rise makes and man healthy, wealthy and wise,” or “An apple a day keeps the doctor away” with this book. One of my favorite quotes was “Keep thy shop, and thy shop will keep the.” It’s one of those books that you can go back to and always find something new. The best part is it’s free and you can probably read the whole thing over your lunch break.


I Will Teach You To Be Rich, Second Edition (2019) – Ramit Sethi

Yeah, the title is sounds scammy but it’s legit. Ramit Sethi goes over all the financial knowledge necessary to build an automated money machine that can help you live a rich life. This book gave me a solid understanding of financial fundamentals to take control of my own finances. Since I didn’t study anything financial in my formal education, it was really helpful to learn about credit card optimization, 401(k)s, Roth IRAs, Health Savings Accounts, Target Date Funds, stocks, and bonds. He even includes scripts to negotiate down interests rates, remove banking fees, and asking for raises. Admittedly, I read the book in two weeks and applied the principles over a four week period but by the end of it, I established my own automated money machine equipped with an emergency fund, multiple savings accounts and a retirement investment portfolio. However, the most important thing I learned from this book is that we can learn how to do anything if we decide to go out and look for the information. Investing my money and learning all the financial jargon seemed out of my depth, but this book showed me that everything can be learned.


On The Shortness of Life (49 AD) – Seneca

I first heard of this book from Maria Popova. She is a fantastic writer and runs a blog (there really should be a different word for what she does) called Brain Pickings. It’s a huge archive of the deepest ideas from an extremely well articulated writer. Maria recommends people to start with her post about this book. I read her post and loved it. Then I read this book and it changed my life. Seneca talks about how there is more time than life. So much more that we actually waste it. How much of our lives are spent trying to answer the question at a dinner party, “so what do you do?” We give most of our time to others and much of the time dedicated to ourselves is in the service of impressing others. It’s no surprised life is exhausting. The key is to take the time back for ourselves. Seneca suggests that if we were to give all the time we were allotted on Earth to ourselves then we would greet death with open arms. This book has given me a damn good reason to let go of the idea that life is short.


The 4-Hour Workweek (2007) – Timothy Ferriss

Oh boy. To be honest, I’m not sure where to start with this book. Read it. It’s literally a manual to escape the 9-5 and live like the new rich. This is the first book I’ve read from Tim Ferriss and I fell in love with it. Tim breaks down what it means to start and automate a business that gives you the money and freedom to live your dream life. Tim started a mega successful online business in his 20s which gave him a pretty solid fortune. However, he was spending literally all of his time working (specifically replying to emails). Tim, being the unique thinker he is, found a way to restructure his business to maximize his efforts and run his company with only a few hours of work a month. This book isn’t literally about cutting your workweek down to 4 hours, its about maximizing the output of the work so you can free yourself up to do the things that really matter. He has ways to increase productivity with lower levels of stress and effort for all types of jobs. Whether you own your own business, work for an idiot boss, or are looking for a way to escape the rat race, this book is a must read. He’s included little “life hacks,” mindset switches, and resources that you may need to start an automated business. Pair this with Ramit Sethi’s just as scammy sounding book I Will Teach You To Be Rich and you have the tools necessary to design and live out your rich life.


Mastery (2012) – Robert Greene

Robert Greene is a powerhouse and heavy hitter when it comes to writing damn good books. This book is a guide to mastering anything. Robert researched masters from all walks of life throughout time and found the common threads between each of them. He covers everyone from Mozart to Charles Darwin to Temple Gradin to Freddie Roach. My favorite person he writes about in this book is Benjamin Franklin. I love how Greene outlines Franklin’s journey to mastery in writing and social interactions. Robert goes above and beyond for this book (as usual) and takes things much further than the typical skill acquisition advice like the 10,000 hour rule or practicing every day. I saw Robert Greene at a book signing and he said that he writes books out of anger. When he wrote this book, he said he was angry that people couldn’t make things well anymore. So I like to think of this book as a guide to learning how to do things well.


The Art of War (~5th Century BC) – Sun Tzu

Perfect reading for learning war strategies on a battlefield. Also perfect reading for MBA types about to enter the business world. Also perfect reading for anyone who finds themselves in adversarial situations. This book is pure wisdom when it comes to war, or anything that can resemble a war. Sun Tzu’s philosophy on war is to win without fighting. Running in head first into a battle is a sure way to get yourself killed, lose resources, and cause long term damage to the state. It’s better to cultivate your defenses, fortify your plans, and only fight when you know you are going to win. This is a quick and short read. The Art of War was originally written for military strategy but that doesn’t mean it can only be applied in the literally battlefield. Much of our encounters and challenges we experience today are war-like and the principles discussed in the book are worth applying to other areas of life. I have a thing for books written mad long ago but are still relevant now. This was written around 5th century BC but the lessons have been true throughout time. Timeless books are the best books.


The 4-Hour Body (2010) – Timothy Ferriss

One of Tim’s main goals in life is to learn something once and never have to learn it again. To make this happen, he takes meticulous notes on his diet, work out, habits, etc. so when he sees a picture of himself years prior he knows exactly what he was doing to get the body he had. He also keeps journals too, so he can do a similar type of assessment with his mental health as well. The combination of his meticulous note taking, years of experimentation, and hours of consulting physicians has given us this unconventional guide to healthier and easier living. Similar to The 4-Hour Workweek, this book is about getting the maximum results for the smallest effort. This book is filled with Minimum Effective Dosages (MEDs) for fat-loss, muscle gain, better sex, better sleep, reversing injuries, and much much more. I highly recommend this book for anyone that wants a guide to the human body.


Letters From A Stoic (65 AD) – Seneca

This book came up in the afterglow of reading On The Shortness Of Life. It’s a collection of letters Seneca wrote to his friend Lucilius. There are 224 letters and each one is on a profound topic. Reading these letters made me feel like I was getting to know Seneca personally. I love his humor and his unapologetic fanboy attitude towards Epicurus. What I loved the most about this book is that it explains Stoic philosophy within the context of something relatable which made it easy to see the usefulness of stoic practices. Wisdom is an art and this book is filled with it. Each letter is short but the ideas introduced will have you thinking about them for years to come. Every time I pick up this book it’s an absolute mindfuck. Seneca was able to articulate some of the most complicated thoughts I have ever had but never been able to say. This book was simultaneously a justification and condemnation of my perspectives and value structures and I love it. This book has wisdom beyond my years and I’m excited to see what else I’ll learn as I read the book with older eyes. This book has an extremely high reread value. Similar to Robert Greene’s The Laws of Human Nature, this is a book that you study – not read.


12 Rules for Life: An Antidote to Chaos (2018) – Dr. Jordan B. Peterson

Let me start by saying if you haven’t checked out Dr. Jordan B. Peterson’s work – check all of it out. This is his 2nd book and it’s more than worth the read but diving into his hours of lectures on YouTube will really take you for a ride. Peterson is a clinical psychologist from Canada who taught at the University of Toronto and Harvard. He’s spent decades studying the world’s best thinkers and reading some of the most complicated and influential texts. And through those studies, he’s articulated the true importance of meaning and responsibility. This book is a small part of that perspective. It originally was a list of 40 rules Peterson wrote in response to a post on Quora: “What are the most valuable things everyone should know?” Peterson cut down the list to 12 and wrote this book. Peterson said that these 12 are not necessarily the most important rules, but they do make a cohesive narrative together.


Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers (2016) – Tim Ferriss

Another Tim Ferriss masterpiece. Tim Ferriss is to me what Epicurus is to Seneca. Tools of Titans was written after Tim’s 4-Hour trilogy. The book was created from a plethora of interviews from The Tim Ferriss Show. Tim interviews the world’s highest performers about their habits, mindsets, and personal quirks that make them successful and put that in this book. He interviews everyone from Jocko Willink to B.J. Novak to Rick Rubin to Sam Harris to Maria Popova. Since there are so many people in this book, it’s easy to look up people that you already admire as well as discover new people to learn from. He breaks up the book in 3 sections (I love that it’s inspired by Ben Franklin): Healthy, Wealthy, and Wise. My favorite chapters were in the Wise section, but that’s just me. There is enough information in this book to build empires and has an extremely high reread value.


Updated October 20th, 2020
The Essays of Arthur Schopenhauer: The Wisdom of Life (1851) – Arthur Schopenhauer

Probably my favorite piece of work from the Great pessimist. I thought the title was too grandiose at first, but Artie delivered. This book truly contains the wisdom of life. There are some things he was pretty off on, but for the most part he was on point. He captures the beauty, rarity, and absurdity of life in a way that doesn’t play them up or down.

I also think this book is great because it’s like a collection of blog posts Schopenhauer would have written if blogs were a think in the 19th century. I’ve already written things in my blog that I don’t completely agree with and I could imagine that if Schopenhauer wasn’t bounded by his time that he would redact some of what he said. When we write down what we know, we are sure to be wrong but I believe it’s worth it to capture the things we got right.

Schopenhauer is a thinker for the ages and I highly suggest this book is someone who wanted to check out his work. He wrote it later in his life so his words carry the wisdom of his past works and it shows.


Games People Play (1969) – Dr. Eric Berne

This fantastic book goes over something called transactional analysis which is the study of how humans interact with each other. Berne suggests that everyone had 3 primary ego states — Child, Adult, and Parent and those ego states communicate with each other. The “games people play” are dependent on which ego state is communicating with what and how they do so. For example, there’s a game refers to as NIGYSOB (Now I’ve Got You Son Of a Bitch) is a game played between one’s parent ego state and the other’s child ego state. I might do a post on the different games mentioned in this book (at least the one’s I’ve found most prevalent) sometime because it’s almost unbelievable how much of human interaction are simply games.

On top of the incredibly deep analysis of human interaction, he sprinkles in humor throughout the book with smart ass comments and witty names for the games. This is book spelled out many ideas that I knew existed, but couldn’t articulate for myself and having access to these ideas gives me a greater understanding of human interaction and a special peace of mind.


The Seagull (1896) – Dr. Anton Chekhov

This is the first play I’ve put on this list and admittedly, the first play I’ve read since my appreciation for literature blossomed. I read this when I was at a point in my life when I felt like I had to choose between pursuing medicine and being creative and I was shocked to discover Anton Chekhov, famed playwright/physician. I first heard of Chekhov in Robert Greene’s Laws of Human Nature and I was so blown away from his story that I had to check out his work.

This play is super short and can easily be read in a few hours. The characters are brilliant and the story is beautiful. It’s a fantastic dramatization of the violence that occurs when a beauty is misplaced. One of the ideas I took from this play was “beautiful creatures in beautiful places will lead to destruction if things are not in their right place.” Chekhov created an excellent depiction of the realities of true rage, the struggles of the creative spirit, and the dangers of not being seen in the hearts and minds of others.

This play also gave me insights into what I was feeling as a creative person. If a Russian playwright could perfectly write about a similar struggle and capture my feelings perfectly, then what I was feeling must have been universal and archetypal. This realization lifted a huge burden on me because I realized that what I was dealing with could be surmounted by man and didn’t have to crush me.

If we’re not careful, we can all be like Treplyov.


The Checklist Manifesto: How to Get Things Right (2009) – Dr. Atul Gawande

I wouldn’t suggest this book to beginner readers, as most things written by doctors are long-form and operate at a certain level of complexity, but if you’re comfortable reading lengthy texts, then this is a great book.

I originally didn’t want to put this book on the list, but as I continued to write my blog and work with my students I’ve noticed how much this book changed my thoughts and actions. Any book that changes how I act and think on a daily basis for the better is worth putting on this list.

I guess that’s precisely what Dr. Gawande was referring to in the book as well — the idea that checklists are so easily overlooked, but also so effective.

Checklists are my primary go-to method for organizing the chaos and getting things done right. They are too simple and too effective to ignore.


Collected Works of C.G. Jung, Volume 9 (Part 1): Archetypes and the Collective Unconscious (1959) – Dr. Carl Gustav Jung

This is the deepest book I’ve ever read. On top of that, Jung is the smartest person I’ve ever had the privilege of reading. He accurately sums up the most abstract and complicated ideas in a concise way that’s easy to understand. Jung believes that humans encounter the experience of the unknown in similar ways, through archetypes. These archetypes are patterns of behavior coded in us from millions of years of human evolution and are the same no matter what society we’re from. The archetypes give us access to the collective unconscious which allows us a greater understanding of the human psyche.

Jung puts this way better than I could and has been a MASSIVE contributor to everything I do. The way I teach and conduct myself in the world is informed through my knowledge and understanding of the collective unconscious.

He doesn’t go into as much detail as I’d like in this volume, but he touched upon his famed archetypal ideas in a way that provides a rudimentary understanding to those who aren’t familiar. He talks in depth (by not deep enough) about the Shadow, the Anima (Great Mother), the Animus (Judgemental Father), and so many more.

This is the only book (so far) that I haven’t finished yet, but I’ve gotten through a good chunk of it. It’s so dense and rich with knowledge and wisdom. I knew that I had to put this book on my list when I was just a few pages in.

This guy sees the edge of human knowledge and goes there. Jung is probably my favorite author of all time. Read this book and get your mind blown.


Man’s Search for Meaning (1946) – Dr. Viktor Frankl

This book changed me life and I cannot understate it’s value. Everyone needs to read this book. It details the horrors of the Holocaust from the perspective of Jewish psychiatrist, Dr. Viktor Frankl. He is an incredible writer and captures such powerful images despite being traumatized himself. The images he describes were vivid and dark, but the lessons he learned about human beings are both beautiful and tragic. This book also outlines a method of created for his medical practice – logotherapy, which is based on the premise that meaning is our fundamental driving force as human beings.

This book is one of the most beautiful pieces of work ever created. Frankl showed us how people can really find meaning, even in the most hopeless situations. Meaning will carry us through any and all suffering.


Self-Reliance (1841) – Ralph Waldo Emmerson

This book is so dope. It’s written in a slightly outdated language, but the message is evergreen and powerful. He talks about the importance of self-reliance, giving to yourself, and the morality of only involving ourselves with the things which concern us.

In a weird way, this book was able to give me the reasoning I lacked to only concern myself with matters that concern me. I used to feel like I couldn’t act purely in my own interests, but this book has shown me that it isn’t only okay to act in my own interests but a moral duty, especially if my interests can make things better for me, my family, and my community.

One of the most amazing parts about it is that this was written while Emmerson was away from society locked up in a cabin in the middle of the woods. Then fast-forward almost 200 years, I’m reading it on an iPad in the comfort of my own bed. This realization had nothing to do with what he wrote, but it speaks to the power of writing. After I read this book, I was able to find the strength within me to write more vigorously and focus on myself and that led to incredibly important groundwork.


The Practicing Mind: Bringing Discipline and Focus Into Your Life (2006) – Thomas M. Sterner

Everything worth achieving requires practice and Thomas M. Sterner gives us techniques to develop the focus and discipline necessary to practice successfully. I’ve written an entire blog post based on the principles from this book that highlights some of the ideas that I thought were the most worth knowing.

Reading this book gave me a much-needed perspective on what it means to practice effectively. It’s so easy to see practicing as work, but after applying the methods Sterner talks about in the book, practice becomes a time full of meaning and purpose. Focusing on the process and intentionally staying present are highly underrated ideas that will bring out the best in anything.


The Personal MBA: Master the Art of Business (2010) – Josh Kaufman

This is a fantastic book on business. Honestly, it could be THE book on business if there was one. It’s cool to see all the fancy business jargon wrapped up all nice and neat and it’s doubly cool to see a book that’s kind of like the book I’ve been writing but in a completely different field.

It’s been a huge influence on me and how I run my business and is a must-read for anyone who’s interested in entrepreneurship. It goes over everything from value creation from marketing to sales to finance to the mind to creating systems and so much more.

I’m constantly finding myself going back to this book. It’s full of amazing information that is extremely useful when starting a business, especially since I never had any formal training. I read it shortly before starting my 1st official company and while I was reading it, I knew that I was going to be going back to it for years to come.

Whether you’re an expert or a beginner in business, this book is a must-read if you want to be intentional about your business.


The Slight Edge (2005) – Jeff Olson

When I first read this book I didn’t think the slight edge could be true because of the sheer simplicity of it, but then I started trying it in my own life.

I think everyone should still read this book (obviously because it’s on this list), but the slight edge as a concept is pretty simple — small disciplines over time is what determines our life outcomes. The good things we do make our life better, the bad things we do make our life worse. These outcomes work on an exponential basis so over time, the successful win more often and the losers lose more often.

The slight edge really is what separates the successful from the failures. Olson says the slight edge is what’s the difference between a beach bum and a multimillionaire because he’s been both.

I’ve also seen Kobe Bryant talk about this being the reason why he was so much better than everyone else in the NBA. He kept pushing when everyone else didn’t. It’s probably a cognitive bias thing, but after I read this book I’ve noticed it in so many places.

Like everyone – this list is forever in a state of becoming.